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Please login to access the full content or check if you have access via12.3.1.4.3.5 Method 5: Reactions of α-Aminonitriles with Aldehydes or Ortho Esters
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Grimmett, M. R., Science of Synthesis, (2002) 12, 380.
When 2,4(5)-disubstituted imidazoles are formed by reaction of 2-aminonitriles with aldehydes, the aldehyde provides the C2 substituent.[235,236] With benzaldehyde, (methylamino)phenylacetonitrile gives 1-methyl-2,5-diphenyl-1H-imidazole in 76% yield.[236] If an orthoformate is used in place of the aldehyde, the products are 1H-imidazol-4(5H)-ones. Thus, refluxing aminoacetonitrile hydrochloride for about 30 minutes with trimethyl orthoformate produces a small amount of 1H-imidazol-4(5H)-one along with (formamido)acetonitrile as the major product.[237,238] As the N-substituted α-aminonitriles can be made rapidly by a mild, one-pot combination of aldehyde, primary or secondary amine, and chlorotrimethylsilane in methanol,[239] this general approach may have further applications.
References
[235] | Meeeeeee, M. M., Mee. Meeee. Meee. Mee., (8888) 88, 8888. |
[236] | Meeee, M.; Meeee, M.; Meeeeeeee, M.; Meeeeee, M., Meee. Mee., (8888) 888, 8888. |
[237] | Meeeeee, M. M., Meeeeee Mee. Meee., (8888), 888. |
[238] | Meeeeeee, M.; Meeeeeeee, M. M.; Meee, M.; Meeee, M., Meeeeee Mee. Meee., (8888), 888. |
[239] | Mee, M.; Meeee, M., Meeee. Meeeee., (8888) 88, 888. |
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- 8.Meeeee-Meee, (8888) M 8e, 88.